Diphenylsilane → Methyl (R)-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

HRID 1875328

反応式

HRID 1875328 の反応式
[CH3:1][N:2]1[C@H:11]([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]([O:15][CH3:16])=[O:14])[CH:8]=2)[C:3]1=O.C1([SiH2]C2C=CC=CC=2)C=CC=CC=1>C1COCC1.[C-]#[O+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Rh]>[CH3:1][N:2]1[C@H:11]([CH3:12])[CH2:10][C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:13]([O:15][CH3:16])=[O:14])[CH:8]=2)[CH2:3]1

参加物

5

反応物 2

HCID 69888Diphenylsilane2 回HCID 86761672methyl (R)-2,3-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

生成物 1

HCID 86761671Methyl (R)-2,3-dimethyl-1,2,3,4-tetrahydroisoquinoline-6-carboxylate

試薬・触媒・溶媒 2

HCID 10941995Carbonylhydridotris(triphenylphosphine)rhodium(I)触媒2 回HCID 8028Tetrahydrofuran溶媒

実験手順

60 mg (257 μmol) methyl (R)-2,3-dimethyl-1-oxo-1,2,3,4-tetrahydroisoquinoline-6-carboxylate are dissolved in 2 ml THF under an argon atmosphere and at RT combined with 100 μl (542 μmol) diphenylsilane. Then 20 mg (21 μmol) carbonylhydridotris(triphenylphosphine)rhodium(I) are added and the mixture is stirred for two hours. A further 50 μl diphenylsilane and 10 mg carbonylhydridotris(triphenylphosphine)rhodium(I) are added and the mixture is stirred for a further 2.5 hours. Then the reaction mixture is evaporated down i. vac. and purified by flash chromatography on silica gel (eluant DCM/MeOH 95:5).

後処理

  1. stirringthe mixture is stirred for a further 2.5 hours
  2. customThen the reaction mixture is evaporated down i
  3. customand purified by flash chromatography on silica gel (eluant DCM/MeOH 95:5)

出典と根拠

ORDレコード
ord-aecf0787748f46eabe57a4dd91f97eba
出典データセット
uspto-grants-2012_11
特許番号
US08309542B2

関連ノート

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